Tetrahydrofuran → HCID 53814882, compound

HRID 2294549Notes

Reaction equation

[H-].[Na+].[C:3]12([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=3[OH:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[CH2:21]1COCC1>>[C:3]12([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=3[O:20][CH3:21])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([CH2:6]3)[CH2:12]1)[CH2:10]2

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 223478532-(1-Adamantyl)-5-bromophenol

Product 1

HCID 53814882HCID 53814882, compound

Procedure

1.6 g (53 mmol) of sodium hydride (80% in oil) and 50 ml of THF are introduced into a round-bottomed flask and a solution of 15 g (49 mmol) of the phenol obtained above in (a), dissolved in 100 ml of DMF, is added dropwise. The mixture is stirred until gaseous evolution has ceased and 3.1 ml (49 mmol) of methyl iodide are then introduced. The mixture is stirred at room temperature for four hours, the reaction medium is poured into water and the organic phase is separated after settling has taken place, then dried over magnesium sulphate and evaporated. The residue obtained is ground in the minimum amount of hexane and filtered off. 12.6 g (80%) of 2-(1-adamantyl)-5-bromoanisole, melting point 159°-160° C., are collected.

Sources & evidence

ORD record: ord-3537e8e596be44409f13b75234fb4c09
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688817

Reaction notes

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